1619967-08-6

Basic information

• Product Name: 5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene
• Synonyms: 5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene
• CAS NO: 1619967-08-6
• Molecular Formula: C8H2Br2F2S2
• Molecular Weight: 360.0362864
• EINECS: -0
• Mol File: 1619967-08-6.mol

Chemical Properties

• Boiling Point: 297.0±35.0 °C(Predicted)
• Appearance: /
• Density: 2.063±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene(1619967-08-6)
• EPA Substance Registry System: 5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene(1619967-08-6)

Safety Data

• Hazardous Substances Data: 1619967-08-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronic Devices:
5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene is utilized as a key component in the fabrication of organic light-emitting diodes (OLEDs) due to its ability to enhance the performance and efficiency of these devices. Its presence in the molecular structure contributes to improved light emission and stability, making it an essential material for display and lighting technologies.
Used in Photovoltaic Cells:
In the photovoltaic industry, 5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene serves as a vital material for the development of high-performance solar cells. Its incorporation into the active layer of these cells aids in capturing and converting sunlight into electricity more effectively, thereby increasing the overall efficiency and power output of the solar panels.
Used in Organic Field-Effect Transistors:
5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene is employed as a semiconductor material in the design of organic field-effect transistors (OFETs). Its unique electronic properties allow for the creation of flexible and lightweight transistors with potential applications in various electronic devices, including sensors, displays, and integrated circuits.
Used in Materials Science Research:
5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene is also used as a subject of study in materials science, where its properties are explored for potential applications in the development of new materials with tailored electronic, optical, and structural characteristics. This research can lead to advancements in various fields, such as nanotechnology, polymer science, and materials engineering.

Upstream product

• 32431-65-5 2-bromo-4-fluorothiophene 
• 207742-50-5 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene 

Downstream Products

• 1619967-09-7 3-fluoro-2-(3-fluoro-5-(trimethylstannyl) thiophen-2-yl)-5-(trimethylstannyl)thiophene 

Relevant articles and documents

Implication of Fluorine Atom on Electronic Properties, Ordering Structures, and Photovoltaic Performance in Naphthobisthiadiazole-Based Semiconducting Polymers

The development of semiconducting polymers is imperative to improve the performance of polymer-based solar cells (PSCs). In this study, new semiconducting polymers based on naphtho[1,2-c:5,6-c′]bis[1,2,5]thiadiazole (NTz), PNTz4TF2 and PNTz4TF4, having 3,3′-difluoro-2,2′-bithiophene and 3,3′,4,4′-tetrafluoro-2,2′-bithiophene, respectively, are designed and synthesized. These polymers possess a deeper HOMO energy level than their counterpart, PNTz4T, which results in higher open-circuit voltages in solar cells. This concequently reduces the photon energy loss that is one of the most important issues surrounding PSCs. The PNTz4TF4 cell exhibits up to 6.5% power conversion efficiency (PCE), whereas the PNTz4TF2 cell demonstrates outstanding device performance with as high as 10.5% PCE, which is quite high for PSCs. We further discuss the performances of the PSCs based on these polymers by correlating the charge generation and recombination dynamics with the polymer structure and ordering structure. We believe that the results provide new insights into the design of semiconducting polymers and that there is still much room for improvement of PSC efficiency.

Fluorination of polythiophene derivatives for high performance organic photovoltaics

For the purpose of examining the tuning of photophysical property by fluorine atom substitution, fluorinated and nonfluorinated poly(3,4- dialkylterthiophenes) (PDATs) were synthesized, and their photovoltaic properties were compared. Fluorinated PDATs exhibit a deeper highest occupied molecular orbital energy level than nonfluorinated ones, leading to higher open-circuit voltage in organic solar cells and also enhanced molecular ordering as evidenced by a vibronic shoulder in UV-vis spectra, π-π scattering in GIWAXS, and a well-developed fibril structure in TEM, which contributes to efficient charge transport. As a result, the fluorine substitution increases the power conversion efficiency by 20% to 250% as compared with nonfluorinated PDATs.

Pd-Catalyzed Aerobic Oxidative Coupling of Thiophenes: Synergistic Benefits of Phenanthroline Dione and a Cu Cocatalyst

Substituted bithiophenes are prominent fragments in functional organic materials, and they are ideally prepared via direct oxidative C-H/C-H coupling. Here, we report a novel PdII catalyst system, employing 1,10-phenanthroline-5,6-dione (phd) as the ancillary ligand, that enables aerobic oxidative homocoupling of 2-bromothiophenes and other related heterocycles. These observations represent the first use of phd to support Pd-catalyzed aerobic oxidation. The reaction also benefits from a Cu(OAc)2 cocatalyst, and mechanistic studies show that Cu promotes C-C coupling, implicating a role for CuII different from its conventional contribution to reoxidation of the Pd catalyst.

Method for Aerobic Oxidative Coupling of Thiophenes with a Ligand-Supported Palladium Catalyst

An oxidative homocoupling method of synthesizing certain 2,2′-bithiophenes from thiophenes using oxygen as the terminal oxidant is disclosed. In non-limiting examples, the method uses oxygen along with a catalytic system that includes palladium, an assistive ligand, and a non-palladium metal additive to catalyze one of the following reactions: Associated catalytic systems and compositions are also disclosed.